bisebromoamide | 1233532-51-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: bisebromoamide
• 英文别名: (4S)-2-[(2S,4S)-1-[(2R)-3-(3-bromo-4-hydroxyphenyl)-2-[[(2S)-2-(2,2-dimethylpropanoylamino)propanoyl]-methylamino]propanoyl]-4-methylpyrrolidin-2-yl]-4-methyl-N-[(2R)-4-methyl-1-[methyl-[(2S)-1-oxo-3-phenyl-1-[(2S)-2-propanoylpyrrolidin-1-yl]propan-2-yl]amino]-1-oxopentan-2-yl]-5H-1,3-thiazole-4-carboxamide
• CAS: 1233532-51-8
• 化学式: C₅₁H₇₂BrN₇O₈S
• 分子量: 1023.14
• InChiKey: XNEWSWFKSIOKDS-NMKCGMRTSA-N

物化性质

• 沸点：
  1115.4±65.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  68
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  214
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  bisebromoamide 在 sodium tetrahydroborate 、 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 50.0h， 生成 (2S)-(1-hydroxypropyl)-pyrrolidine
  参考文献：
  名称：

  Bisebromoamide, a Potent Cytotoxic Peptide from the Marine Cyanobacterium Lyngbya sp.: Isolation, Stereostructure, and Biological Activity

  摘要：

  A novel cytotoxic peptide, termed bisebromoamide (1), has been isolated from the marine cyanobacterium Lyngbya sp. Its planar structure was determined by 1D and 2D NMR spectroscopy. The absolute stereostructure of 1 was determined by chemical degradation followed by chiral HPLC analysis. Bisebromoamide (1) exhibited potent protein kinase inhibition: the phosphorylation of ERK in NRK cells by PDGF-stimulation was selectively inhibited by treatment with 10-0.1 mu M of 1.

  DOI：

  10.1021/ol9020546
• 作为产物：
  描述：

  在 三乙基硅烷 、 N-羟基-7-氮杂苯并三氮唑 、 palladium on carbon 、 三氟化硼乙醚 、 氢气 、 三乙基硼氢化锂 、 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， -78.0~70.0 ℃ 、101.33 kPa 条件下， 反应 69.25h， 生成 bisebromoamide
  参考文献：
  名称：

  Total synthesis and cytotoxicity of bisebromoamide and its analogues

  摘要：

  A highly convergent route for assembling bisebromoamide, its stereoisomers and a simplified analogue has been accomplished, which features connecting its left part and right part via thiazoline ring formation at the final stage. Preliminary biological studies revealed that compounds with both proposed and revised structures, and a simplified analogue have similar potency against the proliferation of HeLa S-3 cell, indicating that the stereochemistry of methylthiazoline part, and methyl group at the 4-methylproline residue in bisebromoamide, have limited influence on its cytotoxicity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.058

文献信息

• Total Synthesis and Stereochemical Reassignment of Bisebromoamide
  作者：Xuguang Gao、Yuqing Liu、Shuqin Kwong、Zhengshuang Xu、Tao Ye

  DOI：10.1021/ol101021v

  日期：2010.7.2

  A revised configurational assignment for the thiazoline moiety of the marine peptide bisebromoamide is proposed and validated by total synthesis.

  提出并修订了海洋肽双溴代酰胺的噻唑啉部分的构型分配，并通过总合成进行了验证。
• Total synthesis and cytotoxicity of bisebromoamide and its analogues
  作者：Wenhua Li、Shouyun Yu、Mingzhi Jin、Hongguang Xia、Dawei Ma

  DOI：10.1016/j.tetlet.2010.11.058

  日期：2011.4

  A highly convergent route for assembling bisebromoamide, its stereoisomers and a simplified analogue has been accomplished, which features connecting its left part and right part via thiazoline ring formation at the final stage. Preliminary biological studies revealed that compounds with both proposed and revised structures, and a simplified analogue have similar potency against the proliferation of HeLa S-3 cell, indicating that the stereochemistry of methylthiazoline part, and methyl group at the 4-methylproline residue in bisebromoamide, have limited influence on its cytotoxicity. (C) 2010 Elsevier Ltd. All rights reserved.
• Bisebromoamide, a Potent Cytotoxic Peptide from the Marine Cyanobacterium <i>Lyngbya</i> sp.: Isolation, Stereostructure, and Biological Activity
  作者：Toshiaki Teruya、Hiroaki Sasaki、Hidesuke Fukazawa、Kiyotake Suenaga

  DOI：10.1021/ol9020546

  日期：2009.11.5

  A novel cytotoxic peptide, termed bisebromoamide (1), has been isolated from the marine cyanobacterium Lyngbya sp. Its planar structure was determined by 1D and 2D NMR spectroscopy. The absolute stereostructure of 1 was determined by chemical degradation followed by chiral HPLC analysis. Bisebromoamide (1) exhibited potent protein kinase inhibition: the phosphorylation of ERK in NRK cells by PDGF-stimulation was selectively inhibited by treatment with 10-0.1 mu M of 1.